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Organic synthesis Flashcards

1
Q
A
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2
Q

What is the order of priority when naming molecules

A

Cool Angry Elephants Act Awfully Naughty After Kicking All Angry Animals

Highest priority
Carboxylic acid
> Anhydride
> Ester
> Acyl chloride
> Amide
> Nitrile
> Aldehyde
> Ketone
> Alcohol
> Amine
Lowest priority

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3
Q

What temperature are hydrocarbons heated to in a fractional distillation column

A

350 degrees C

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4
Q

What are the conditions for thermal cracking

A

1000 degrees C
70atm

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5
Q

What are the conditions for catalytic cracking

A

450 degrees C
Zeolite catalyst
Moderate pressure (150kPa)

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6
Q

What is the name of the mechanism whereby hydroxide ions react with a halogenoalkane using an aqueous solvent

A

Nucleophilic substitution

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7
Q

What are the conditions required for the substitution reaction of hydroxide ions with a halogenoalkane

A

Warm aqueous NaOH
Carried out under reflux

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8
Q

What is formed when hydroxide ions react with a halogenoalkane using an aqueous solvent

A

An alcohol

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9
Q

What is formed when halogenoalkanes react with cyanide ions

A

Nitriles

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10
Q

What are the conditions required for the reaction of cyanide ions with a halogenoalkane

A

Warm ethanolic, aqueous potassium cyanide
Carried out under reflux

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11
Q

What are the conditions required for the reaction between ammonia and a halogenoalkane when the desired product is an amine

A

Heat with ethanolic ammonia
Must have excess ammonia

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12
Q

What is produce when ammonia reacts with a halogenoalkane

A

An amine and an ammonium ion

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13
Q

What is the name of the mechanism where hydroxide ions react with a halogenoalkane using an ethanol solvent

A

Elimination

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14
Q

What are the conditions required for the elimination reaction between hydroxide ions and a halogenoalkane

A

Hot ethanolic concentrated sodium hydroxide
Carried out under reflux

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15
Q

When reacting NaOH with a halogenoalkane, when do we form an alcohol

A

When water is used as the solvent

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16
Q

What occurs in the initiation stage of the formation of chlorine radicals which catalyse the breakdown of ozone

A

Sunlight (UV) breaks down the C-Cl bond in a CFC producing 2 radicals which react with ozone molecules

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17
Q

What 2 equations occur in the propagation stage of the formation of chlorine radicals which catalyse the breakdown of ozone

A

1- Cl radical reacts with O3 to form a ClO radical intermediate and O2
2 - ClO radical reacts with more O3 to make O2 and a Cl radical (reformed so is a catalyst)

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18
Q

What occurs in the termination stage of the formation of chlorine radicals which catalyse the breakdown of ozone

A

Two Cl radicals react to form Cl2

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19
Q

Does a higher temperature encourage elimination or substitution for the reaction between OH- and halogenoalkanes

A

Higher temperatures encourage elimination

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20
Q

Does a higher concentration of OH- encourage elimination or substitution for the reaction between OH- and halogenoalkanes

A

Higher concentrations favour elimination.

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21
Q

What mechanism can alkenes undergo when they react with an electrophile

A

Electrophilic addition

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22
Q

What is the test for alkenes

A

When we add bromine water, if alkenes are present, a colour change will occur from brown/orange to colourless

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23
Q

What do we form when we add bromine to an alkene

A

A dibromoalkane

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24
Q

By what mechanism does bromine react with an alkene

A

Electrophilic addition

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25
Q

What is formed when an alkene reacts with a hydrogen halide

A

Halogenoalkanes

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26
Q

What are the conditions for the reaction of bromine with an alkene

A

Room temperature (not in UV light)

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27
Q

What are the conditions for the reaction of hydrogen halides with an alkene

A

Room temperature

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28
Q

What is the role of sulfuric acid when reacting with an alkene

A

Used as a catalyst in making alcohol from an alkene

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29
Q

What do we form when we react sulfuric acid with an alkene

A

Alkyl hydrogen sulfate intermediates
And alcohol as product

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30
Q

What are the conditions for the reaction between an alkene and sulfuric acid

A

Cold, concentrated sulfuric acid

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31
Q

What can we add to an alkyl hydrogen sulfate to reform sulfuric acid, what is this process called

A

Cold water
Hydrolysis

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32
Q

What are the conditions required for the hydrolysis of an alkyl hydrogen sulfate

A

Add cold water to warm a warm alkyl hydrogen sulfate

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33
Q

How can we sustainably make an alkene from an alcohol

A

Dehydrate an alcohol which is produced via the fermentation of glucose from plants in the presence of an acid catalyst

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34
Q

What do we call the process of eliminating water from a molecule

A

Dehydration

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35
Q

How can we form an alcohol from an alkene

A

Hydrate the alkene in the presence of an acid catalyst

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36
Q

Give an equation for the dehydration of ethanol to produce an alkene

A

Must be done in warm conditions (under reflux) and in the presence of concentrated sulfuric acid

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37
Q

What is the mechanism by which the dehydration of alcohols to form an alkene occurs

A

Acid catalysed elimination

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38
Q

When we dehydrate an alcohol, the mixture is impure. What are the components of this impure mixture

A

Alkene
Alcohol
Water
Acid

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39
Q

How can we separate an impure mixture produced from the dehydration of an alcohol

A

Distillation

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40
Q

What can we do to further purify an impure mixture produced from the dehydration of an alcohol which has already been distilled

A

We can use a separation funnel to separate aqueous and organic layers
The addition of a drying agent ( to remove any H2O)

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41
Q

What are the 3 steps in producing cyclohexene from an alcohol

A

Distillation
Separation
Purification

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42
Q

What is the reagent and conditions required for the dehydration of an alcohol to form an alkene, and what is the name of the mechanism

A

Elimination
Reagent: Concentrated sulfuric acid
Conditions: Warm (under reflux)

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43
Q

What are the conditions required for the hydration of ethene to form ethanol

A

high temperature 300 °C
high pressure 70 atm
strong acidic catalyst of conc H3PO4

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44
Q

Outline and name the mechanism for the formation of ethanol via the hydration of ethene

A

Electrophilic Addition

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45
Q

What are the 2 ways of producing ethanol

A

Hydration of ethene (from crude oil)
Fermentation of glucose

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46
Q

What are the conditions for the fermentation of glucose

A

Yeast
Anaerobic conditions
Temperature of 30-40 degrees C

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47
Q

Write equations displaying how ethanol produced by fermentation is a carbon neutral process

A
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48
Q

What 3 things can alcohols be oxidised to form

A

Aldehydes
Ketones
Carboxylic acids

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49
Q

What is the conditions and reagent required for the oxidation of primary alcohols to produce a carboxylic acid

A

Reagent: potassium dichromate(VI) solution and dilute
sulfuric acid
Conditions: use an excess of dichromate, and heat
under reflux (can then distil to separate products)

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50
Q

What is the conditions and reagent required for the oxidation of secondary alcohols to produce a ketone

A

Reagent: potassium dichromate(VI) solution and dilute
sulfuric acid
Conditions: use an excess of dichromate, and heat
under reflux

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51
Q

What is the conditions required for the oxidation of primary alcohols to produce an aldehyde

A

Reagent: potassium dichromate(VI) solution and dilute
sulfuric acid
Conditions: Do not use an excess of dichromate, or heat
under reflux

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52
Q

What is the test for carboxylic acids

A

Addition of sodium carbonate. It will fizz and produce
carbon dioxide if a carboxylic acid is present

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53
Q

What 2 things can we use to distinguish between aldehydes and ketones

A

Fehling’s solution
Tollens reagent

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54
Q

What is the role of both Fehling’s solution and Tollens reagent reagent when distinguishing between aldehydes and ketones

A

They are oxidising agent
They oxidise aldehydes but not ketones

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55
Q

What is the formula for tollens reagent

A

(Ag(NH3)2)+

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56
Q

What is the test for alcohols

A

Acidified K2Cr2O7 goes from orange to green in OH-

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57
Q

What is the reagent and positive test result for primary and secondary alcohols

A

Reagent: acidified pottasium dichromate (K₂Cr₂O₇)
Primary and secondary alcohols are oxidised by K₂Cr₂O₇.
Will turn from orange to green (Cr₂O₇²⁻ to Cr³⁺)

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58
Q

What is the reagent and positive test result for a tertiary alcohol

A

Will remain orange on addition of acidified potassium dichromate

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59
Q

What is the reagent and positive test result for an aldehyde

A

Reagent: Fehling’s solution (in hot water bath) - goes from a blue solution to a red precipitate in the presence of an aldehyde
or
Reagent: Tollens reagent (in hot water bath)- formation of a silver mirror in the presence of an aldehyde

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60
Q

What is the reagent and positive test result for a carboxylic acid
Write an equation for the positive test with CH3CO2H

A

Reagent: Add sodium carbonate
Effervescence of CO2 formed - can then bubble through limewater to test this
2CH3CO2H + Na2CO3 —. 2CH3CO2Na + H2O + CO2

61
Q

What is the reagent and positive test result for chloroalkanes

A

Reagent: Warm with silver nitrate
Slow formation of white precipitate AgCl

62
Q

Write an equation for the reaction of CH3CHO with tollens. Write the practical steps to test it and what occurs

A

Tollens’ Reagent formed by mixing aqueous
ammonia and silver nitrate, which we heat gently in a water bath then add what were testing

Aldehydes are oxidised by tollens into a carboxylic acid, and silver ions are reduced to silver atoms (silver mirror)

CH3CHO + 2Ag+ + H2O —> CH3COOH + 2Ag + 2H+

63
Q

Write an equation for the reaction of CH3CHO with Fehlings. Write the practical steps to test it and what occurs

A

We heat gently in a water bath then add what we are testing

Aldehydes are oxidised by Fehling’s Solution
into a carboxylic acid. The copper (II) ions are reduced
to copper(I) oxide (blue to brick red)

CH3CHO + 2Cu2+ + 2H2O —-> CH3COOH + Cu2O + 4H+

64
Q

Where is the fingerprint region in infrared spectrometry

A

Between 500cm-1 and 1500cm-1

65
Q

What is the condition for optical isomerism to arise in organic compounds

A

The presence of a chiral carbon which gives rise to a non superimposable mirror image

66
Q

How is a racemic mixture formed

A

The carbonyl group is planar
So there is an equal probability of a nucleophilic attack from either side
This leads to the formation of a racemic mixture

67
Q

What does optical activity mean

A

Ability to rotate plane polarised light

68
Q

What are the conditions for EZ isomerism to arise

A

C=C can’t rotate
Each carbon in double bond has 2 different groups attached

69
Q

What are aldehydes oxidised into and what are the conditions and reagent for this reaction

A

Carboxylic acids
Reagent: potassium dichromate (VI) solution and
dilute sulphuric acid.
Conditions:
Heat under reflux

70
Q

How do we make tollens

A

Add a few drops of NaOH to a solution of silver nitrate (forms a pale brown precipitate)
Add a few drops of dilute ammonia until the precipitate dissolves
This is tollens reagent

71
Q

What are the conditions and positive test result for distinguishing between aldehydes and ketones using Fehling’s

A

Conditions: heat gently
Observation: Aldehydes :Blue Cu 2+ ions in solution
change to a red precipitate of Cu2O. Ketones do
not react.

72
Q

What do we use as a reducing agent when reducing aldehydes and ketones

A

NaBH4
Represented as [H]
Source of hydride (H-) ions

73
Q

What is the name of the mechanism by which aldehydes and ketones are reduced using NaBH4

A

Nucleophilic addition

74
Q

What are carbonyl compounds reduced to by CN- ions

A

Hydroxynitriles

75
Q

What is the name of the mechanism by which carbonyl compounds are reduced to hydroxynitriles

A

Nucleophilic addition

76
Q

What are the 2 methods of reducing a carbonyl compound to a hydroxynitrile. State the reagent and conditions for both

A

Method 1:
Reagent: HCN
Conditions: None

Method 2:
Reagent KCN
Conditions: Dilute H2SO4(aq) (Source of H+)

78
Q

Outline 3 stages in how we can measure the melting point of a sample to test its purity

A

Put sample in suitable capillary in oil bath or melting point apparatus
Heat slowly to establish melting point range
Broad range of melting point indicates
presence of impurities
OR melting point agrees with/close to data book value

79
Q

What are the conditions for the reaction between a carboxylic acid and an alcohol to form an ester

A

Concentrated H2SO4 catalyst
Warm conditions (reflux)

80
Q

What is the general equation for the hydrolysis of an ester in acidic conditions

A

Ester + water <—> carboxylic acid + alcohol

81
Q

What is the general equation for the hydrolysis of an ester in alkaline conditions

A

Ester + sodium hydroxide —-> carboxylate salt + alcohol

82
Q

What are the conditions for the hydrolysis of an ester in acidic conditions

A

Dilute H2SO4 catalyst
Hot conditions (reflux)

83
Q

What are the conditions for the hydrolysis of an ester in alkaline conditions

A

Aqueous NaOH
Reflux

84
Q

How do we turn a carboxylate salt from the hydrolysis of an ester in alkaline conditions into a carboxylic acid

A

Add dilute HCl

85
Q

What are the conditions for the reaction between a carboxylate salt and HCl to form a carboxylic acid

A

Warm carboxylate salt
Dilute HCl

86
Q

What do we get when we react glycerol and fatty acids together

87
Q

What do we get when we react NaOH with a fat(ester)

A

Glycerol & soap

88
Q

What is the general equation for saponification

A

Fat + 3NaOH —> Glycerol + 3 Carboxylate salt (soap)

89
Q

What are the conditions for saponification

A

Reflux
Aqueous NaOH

90
Q

What is the general equation for transesterification

A

Fat + 3Methanol —> glycerol + 3Biodiesel (methyl ester)

91
Q

What are the conditions for transesterification

A

KOH catalyst

92
Q

What is the general equation for when an acyl chloride reacts with water

A

Acyl chloride + water —> carboxylic acid + HCl
RCOCl + H2O —> RCOOH + HCl

93
Q

What is the general equation for when an acyl chloride reacts with ammonia

A

Acyl chloride + ammonia —> Amide + HCl
RCOCl + NH3—> RCONH2 + HCl

94
Q

What is the general equation for when an acyl chloride reacts with an alcohol

A

Acyl chloride + alcohol —> Ester + HCl

95
Q

What is the general equation for when an acyl chloride reacts with a primary amine

A

Acyl chloride + primary amine —> N-substituted amide + HCl

96
Q

What is the general equation for when an acid anhydride reacts with a water

A

Acid anhydride + water –> 2carboxylic acid
(2 of the same carboxylic acid)

97
Q

What is the general equation for when an acid anhydride reacts with ammonia

A

Acid anhydride + ammonia –> Amide + carboxylic acid

98
Q

What is the general equation for when an acid anhydride reacts with an alcohol

A

Acid anhydride + alcohol —> Ester + carboxylic acid

99
Q

What is the general equation for when an acid anhydride reacts with a primary amine

A

Acid anhydride + primary amine —> N-substituted amide + carboxylic acid

100
Q

What are the 2 tests for distinguishing between an acyl chloride and an acid anhydride.
For each state the reagent, observation and equation

A

Test 1:
Reagent: H2O
Observation with acyl chloride: Steamy misty fumes due to HCl
Observation with acid anhydride: no visible change
Equation with acyl chloride: RCOCl + H2O –> RCOOH + HCl

Test 2:
Reagent: AgNO3(aq)
Observation with acyl chloride: White ppt due to AgCl
Observation with acid anhydride: no visible change
Equations with acyl chloride: RCOCl + H2O –> RCOOH + HCl
HCl —> H+ + Cl-
Ag+ + Cl- —> AgCl

101
Q

How do we make aspirin

A

salicylic acid + ethanoic anhydride —> aspirin + ethanoic acid

102
Q

What is the most common form of drying agent (when we have a general organic sample and want to remove H2O)

A

Sulfates (Calcium sulfate most common)

103
Q

What is saponification essentially

A

Base hydrolysis of an ester

104
Q

What are the 2 electrophiles which can react with benzene in electrophilic substitution

A

Nitronium ion (NO2+)
Acylium ion (RCO+)

105
Q

What is the name of the mechanism for the nitration of benzene

A

Electrophilic substitution

106
Q

What is the name of the mechanism for the acylation of benzene

A

Electrophilic substitution

107
Q

What are the 3 stages in either nitration or acylation of benzene

A

1- Generation of electrophile
2- Mechanism
3 - Regeneration of catalyst

108
Q

What catalyst is used in the acylation of benzene?

109
Q

What is the reagent, catalyst and conditions required for the acylation of benzene

A

Reagent: RCOCl
Catalyst: AlCl3
Conditions: Anhydrous conditions, reflux, 50 degrees C

110
Q

What catalyst is used in the nitration of benzene?

111
Q

What is the reagent, catalyst and conditions required for the nitration of benzene

A

Reagent: Concentrated HNO3
Catalyst: Concentrated H2SO4
Conditions: Room temperature and pressure

112
Q

What is the name of the molecule produced from the nitration of benzene

A

Nitrobenzene

113
Q

What is the general name of the molecule produced from the acylation of benzene

A

Phenylketone

114
Q

What are the 2 parts to Buchner apparatus

A

Buchner flask
Buchner funnel

115
Q

What are the 2 ways to make a primary aliphatic amine

A

1: Reacting a halogenoalkane in excess NH3
2: Reducing a nitrile

116
Q

What are the reagent and conditions required for the amine nucleophilic substitution reactions

A

Reagent: Concentrated NH3
Conditions: High pressure & heat in a sealed container

117
Q

What does using an excess of NH3 in the amine nucleophilic substitution reactions lead to

A

An excess of NH3 minimises further substitution

118
Q

What does using an excess of halogenoalkanes in the amine nucleophilic substitution reactions lead to

A

Excess of halogenoalkanes favours further substitution

119
Q

What are the conditions and reagent for method 1(using LiAlH4) of producing a primary aliphatic amine through the reduction of a nitrile

A

Reagent: LiAlH4
Condition: In dry ether

120
Q

What are the conditions and reagent for method 2 (catalytic hydrogenation) of producing a primary aliphatic amine through the reduction of a nitrile

A

Catalytic hydrogenation

Reagent: H2
Conditions: 150 degrees C
Catalyst: Nickel catalyst

121
Q

What are the 2 methods to prepare an aromatic amine (NITROBENZENE TO PHENYLAMINE)

A

NITROBENZENE TO PHENYLAMINE

Method 1: Using a reducing agent
Method 2: Catalytic hydrogenation

122
Q

What are the 2 methods to prepare a primary aliphatic amine from the reduction of a nitrile

A

Method 1: Using Lithium aluminium hydride
Method 2: Catalytic hydrogenation

123
Q

What are the reagent and conditions for method 1 (using a reducing agent) of preparing an aromatic amine in both a lab and industry

A

Lab:
Reagent: Concentrated HCl
Catalyst: Sn

Industry:
Reagent: Concentrated HCl
Catalyst: Fe

Both under reflux

126
Q

What are the monomers of kevlar

A

Benzene-1,4-dioic acid
Benzene-1,4-diamine

127
Q

What are the monomers of nylon-6,6

A

Hexane-1,6-dioc acid
Hexane-1,6-diamine

128
Q

What are the monomers of terylene

A

Benzene-1,4-dioc acid
Ethane-1,2-diol

129
Q

How do disulphide bonds arise

A

Thoil groups (-SH) can lose the H atom and the sulfur atoms can bond forming a disulphide (S-S) bond

130
Q

What two factors affect the effectiveness of an inhibitor

A

Concentration of inhibitor
How strongly the inhibitor binds to the active site of an enzyme

131
Q

What type of method is used when developing new drugs

A

Trial and error
Scientists will see which inhibitors work and refine the molecule to make it more efficient

132
Q

What are the monomers of DNA

A

Nucleotides

133
Q

What are the 3 components which make up a nucleotide

A

A phosphate
A sugar
A base

134
Q

What are the reagent and conditions for acid hydrolysis

A

Reagent: Aqueous HCl
Conditions: Reflux

135
Q

Write how many H bonds form between A-T & C-G

A

Adenine (A) pairs with Thymine (T) → 2 hydrogen bonds

Guanine (G) pairs with Cytosine (C) → 3 hydrogen bonds

136
Q

Colour code the bonds between A-T & C-G

137
Q

What are the 2 solvents used in NMR

138
Q

Draw the structure of CDCl3

139
Q

Draw the structure of CCl4

140
Q

What are the components of the moving phase in TLC?

A

Solvent

The solvent carries the samples up the TLC plate.

141
Q

What is the stationary phase in TLC made of?

A

Silica gel or alumina on aluminum, glass, or plastic

The stationary phase interacts with the compounds being separated.

142
Q

What is another method to visualize TLC spots besides UV?

A

Using a stain or developing agent like ninhydrin

143
Q

What is the moving phase in gas chromatography (GC)?

A

Carrier gas (e.g., He or N₂)

144
Q

What is the stationary phase in GC?

A

Non-volatile liquid film on inert powder in a coiled tube

145
Q

What is the stationary phase in column chromatography?

A

Silica or alumina powder

146
Q

What is the moving phase in column chromatography?

A

Eluent (a pure solvent or mixture)

147
Q

Generally, when is it dilute Vs conc H2SO4 as a condition

A

When H2SO4 is a catalyst it is conc, otherwise it tends to be dilue
(Apart from acid hydrolysis)

148
Q

What are the conditions for base/acid hydrolysis of a peptide (or ester)

A

Base : Aqueous NaOH under reflux
Acid: Aqueous dilute H2SO4 under reflux

149
Q

Why do amino acids separate on a TLC plate
(The 1 liner to remember)

A

Difference in the balance between solubility in the mobile phase and attraction to the stationary phase

Chemistry (Organic) (16 decks)

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